Back in the alley, the only trace of Benny that remains is a puddle of blood on the ground. The rest of him has been tucked into the trunk of the Impala along with the knife that cut him from this mortal coil. Hopefully Dean doesn't get stopped along the way for speeding, right? As the Impala rumbles down the road, the homeless man from earlier watches with interest. His eyes go black to let us know he's Crowley's tattletale demon.
One scene later and Benny & the Jerks have already reached the portal. Maybe they've been traveling for hours, but even that would be a ridiculously short journey. Remember how many flashbacks it took for Castiel, Dean and Benny to get there? Remember how many monsters they had to fight? In contrast, this trip has seemed like a walk through the park. I mean that literally. Throw in a bench of two and it's a park with a handful of miscreants and muggers. Sam rolls up his sleeve and explains to Bobby. "We get to Earth and I release you, it's an express straight to Heaven. No time for goodbyes." Bobby once again hints that he'll be back. Please let that be wishful thinking and not foreshadowing. Please let somebody stay dead for once. They each gash their arms with the Demon Knife, then clasp forearms while Sam mutters some Latin. Bobby disappears into Sam's wound. "All right, Benny, it's your turn," Sam says, holding out the knife. Benny makes no move to take it from him.
Three more monsters advance on them from the woods. One guy chastises Benny for working with a Winchester again. "Hurry," Sam says. "Time for you to go," Benny says, patting him on the shoulder. "Go on, it's me they want," he says. "Just make sure you tell Dean I said goodbye. I was never any good up there anyway." Sam tosses him the P-knife and Benny throws himself into the fight while Sam clambers up to the portal. He pauses to call out to Benny one last time, then the portal whisks him away.
He comes out the other end in 100-Mile Wilderness, Maine, as Dean did in the first episode. How lucky they are that the portal leads to somewhere in America, and not, say, a polar icecap, or Mercury, or the Serengeti in the middle of a pride of lions. Dean, who's been pacing and fretting in the dark woods, grabs Sam for a hug. They hug and hug and then pull away. "Purgatory's a real garden spot, ain't it?" Dean asks. "Yeah," Sam agrees. "Did you get 'em out?" Dean asks. "Only Bobby," Sam says, looking truly heartbroken about it. Dean looks like he's been punched hard enough to knock the wind out of him. Sam explains that Benny used himself as bait, and that he didn't seem to want to escape anyway. "I'm sorry," Sam says. "You're probably right," Dean says. He's broken up about it, but we're almost out of time, so he moves on to the subject of Bobby.